肌氨酸TMS酯 | 5269-39-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 肌氨酸TMS酯
• 英文名称: sarcosine trimethylsilyl ester
• 英文别名: O-(Trimethylsilyl)sarcosine；sarcosine TMS ester；N-Methyl-glycin-trimethylsilylester；Sarkosin-trimethylsilylester；Trimethylsilyl 2-(methylamino)acetate
• CAS: 5269-39-6
• 化学式: C₆H₁₅NO₂Si
• 分子量: 161.276
• InChiKey: ODZFTUSXFKBJHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 8-oxooct-4-en-2-ynoate 、 肌氨酸TMS酯 以 甲苯 为溶剂， 反应 1.0h， 以20%的产率得到ethyl 1-methyl-2,6,7,7a-tetrahydro-1H-indole-3-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones

  摘要：

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.

  DOI：

  10.1021/jo901978y
• 作为产物：
  描述：

  肌氨酸 、 六甲基二硅氮烷 以 甲苯 为溶剂， 生成 肌氨酸TMS酯
  参考文献：
  名称：

  Ruehlmann,K. et al., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 32, p. 37 - 42

  摘要：

  DOI：

文献信息

• Isostearyl Mixed Anhydrides for the Preparation of <i>N</i>-Methylated Peptides Using <i>C</i>-Terminally Unprotected <i>N</i>-Methylamino Acids
  作者：Haruaki Kurasaki、Akihiro Nagaya、Yutaka Kobayashi、Ayumu Matsuda、Masatoshi Matsumoto、Koki Morimoto、Tomonori Taguri、Hisayuki Takeuchi、Michiharu Handa、Douglas R. Cary、Naoki Nishizawa、Keiichi Masuya

  DOI：10.1021/acs.orglett.0c02984

  日期：2020.10.16

  Sustainable and efficient manufacturing methods for N-methylated peptides remain underexplored despite growing interest in therapeutic N-methylated peptides within the pharmaceutical industry. A methodology for the coupling of C-terminally unprotected N-methylamino acids mediated by an isostearic acid halide (ISTAX) and silylating reagent has been developed. This approach allows for the coupling of

  尽管制药行业对治疗性N-甲基化肽的兴趣日益浓厚，但N-甲基化肽的可持续和高效制造方法仍未得到充分探索。已经开发了一种由异硬脂酰卤 (ISTAX) 和甲硅烷基化试剂介导的C-末端未保护N-甲基氨基酸的偶联方法。这种方法允许在温和条件下以高产率偶联多种氨基酸和肽，而无需在C的过程中进行C端脱保护步骤-末端伸长。这些优点使其成为生产含有N-甲基氨基酸的肽治疗剂和诊断剂的有用合成方法。
• Formal and total synthesis of (±)-cycloclavine
  作者：Nitinkumar D. Jabre、Teruki Watanabe、Matthias Brewer

  DOI：10.1016/j.tetlet.2013.10.152

  日期：2014.1

  A ring fragmentation and intramolecular azomethine ylide 1,3-dipolar cycloaddition sequence of reactions was successfully used in the preparation of a known (+/-)-cycloclavine precursor in good overall yield. Results of efforts to incorporate the tetrasubstituted cyclopropane ring present in cycloclavine are also discussed. (C) 2013 Elsevier Ltd. All rights reserved.
• The stabilized iminium ylide-olefin [3+2] cyloaddition reaction. Total synthesis of Sceletium alkaloid A4
  作者：Pat N. Confalone、Edward M. Huie

  DOI：10.1021/ja00335a051

  日期：1984.11
• Ruehlmann,K. et al., Journal fur praktische Chemie (Leipzig 1954), 1966, vol. 32, p. 37 - 42
  作者：Ruehlmann,K. et al.

  DOI：——

  日期：——
• An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones
  作者：Cristian Draghici、Qiufeng Huang、Matthias Brewer

  DOI：10.1021/jo901978y

  日期：2009.11.6

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.